IE46988B1 - 2-phenoxymethyl-imidazoline derivatives - Google Patents

2-phenoxymethyl-imidazoline derivatives

Info

Publication number: IE46988B1
Authority: IE; Ireland
Prior art keywords: compound; compounds; medicament; formula; reacting
Prior art date: 1977-06-13

Application number

IE1169/78A

Other languages

English (en)

Other versions

IE781169L (en

Original Assignee

Synthelabo

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1977-06-13

Filing date

1978-06-09

Publication date

1983-11-16

1978-06-09 Application filed by Synthelabo filed Critical Synthelabo

1978-12-13 Publication of IE781169L publication Critical patent/IE781169L/xx

1983-11-16 Publication of IE46988B1 publication Critical patent/IE46988B1/en

Links

GRMJZZBFHKTYDJ-UHFFFAOYSA-N 2-(phenoxymethyl)-4,5-dihydro-1h-imidazole Chemical class N=1CCNC=1COC1=CC=CC=C1 GRMJZZBFHKTYDJ-UHFFFAOYSA-N 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims abstract description 26
150000003839 salts Chemical class 0.000 claims abstract description 8
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 3
239000002253 acid Substances 0.000 claims description 5
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
VLLSCJFPVSQXDM-UHFFFAOYSA-N 2-phenoxyacetonitrile Chemical class N#CCOC1=CC=CC=C1 VLLSCJFPVSQXDM-UHFFFAOYSA-N 0.000 claims description 4
239000000203 mixture Substances 0.000 claims description 4
GHCCHMFFNHOXEU-UHFFFAOYSA-N 2-(chloromethyl)-4,5-dihydro-1H-imidazole hydrochloride Chemical compound Cl.ClCC1=NCCN1 GHCCHMFFNHOXEU-UHFFFAOYSA-N 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
HVCCFMAPGCBCHZ-UHFFFAOYSA-N 2-aminoethylazanium;4-methylbenzenesulfonate Chemical compound NCCN.CC1=CC=C(S(O)(=O)=O)C=C1 HVCCFMAPGCBCHZ-UHFFFAOYSA-N 0.000 claims description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
206010047139 Vasoconstriction Diseases 0.000 claims description 2
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical group [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
239000003085 diluting agent Substances 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims description 2
230000025033 vasoconstriction Effects 0.000 claims description 2
238000000034 method Methods 0.000 claims 5
239000003814 drug Substances 0.000 claims 3
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 claims 1
230000001939 inductive effect Effects 0.000 claims 1
239000007923 nasal drop Substances 0.000 claims 1
229940100662 nasal drops Drugs 0.000 claims 1
239000007922 nasal spray Substances 0.000 claims 1
229940097496 nasal spray Drugs 0.000 claims 1
150000002462 imidazolines Chemical class 0.000 abstract description 4
230000003639 vasoconstrictive effect Effects 0.000 abstract description 3
206010028735 Nasal congestion Diseases 0.000 abstract description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
230000000694 effects Effects 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
241000283973 Oryctolagus cuniculus Species 0.000 description 4
210000000709 aorta Anatomy 0.000 description 4
241000700159 Rattus Species 0.000 description 3
239000000155 melt Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229960005016 naphazoline Drugs 0.000 description 3
229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 description 3
RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
-1 2- (2 - Cyclopentylphenoxy) - methylimidazoline Chemical compound 0.000 description 2
WVCPIDFKPPPYRA-UHFFFAOYSA-N 2-(2-cyclohexylphenoxy)-1-methyl-4,5-dihydroimidazole Chemical compound C1(CCCCC1)C1=C(OC=2N(CCN2)C)C=CC=C1 WVCPIDFKPPPYRA-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
230000008602 contraction Effects 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
239000013081 microcrystal Substances 0.000 description 2
238000010992 reflux Methods 0.000 description 2
206010039083 rhinitis Diseases 0.000 description 2
239000002904 solvent Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000005526 vasoconstrictor agent Substances 0.000 description 2
DCAIEYUJOVJWCG-UHFFFAOYSA-N 2-cyclobutylphenol Chemical compound OC1=CC=CC=C1C1CCC1 DCAIEYUJOVJWCG-UHFFFAOYSA-N 0.000 description 1
MVRPPTGLVPEMPI-UHFFFAOYSA-N 2-cyclohexylphenol Chemical compound OC1=CC=CC=C1C1CCCCC1 MVRPPTGLVPEMPI-UHFFFAOYSA-N 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
206010020772 Hypertension Diseases 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000001186 cumulative effect Effects 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
238000005507 spraying Methods 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/20—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D233/22—Radicals substituted by oxygen atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Cardiology (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Heart & Thoracic Surgery (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

IE1169/78A 1977-06-13 1978-06-09 2-phenoxymethyl-imidazoline derivatives IE46988B1 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
FR7717990A FR2394532A1 (fr)	1977-06-13	1977-06-13	Derives d'imidazoline et leur application en therapeutique

Publications (2)

Publication Number	Publication Date
IE781169L IE781169L (en)	1978-12-13
IE46988B1 true IE46988B1 (en)	1983-11-16

Family

ID=9192012

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IE1169/78A IE46988B1 (en)	1977-06-13	1978-06-09	2-phenoxymethyl-imidazoline derivatives

Country Status (17)

Country	Link
JP (1)	JPS545975A (da)
AU (1)	AU515492B2 (da)
BE (1)	BE867984A (da)
CA (1)	CA1094566A (da)
CH (1)	CH635081A5 (da)
DE (1)	DE2825388A1 (da)
DK (1)	DK258778A (da)
FR (1)	FR2394532A1 (da)
GB (1)	GB1572689A (da)
IE (1)	IE46988B1 (da)
IT (1)	IT1095286B (da)
LU (1)	LU79794A1 (da)
NL (1)	NL7806269A (da)
NO (1)	NO782027L (da)
NZ (1)	NZ187507A (da)
SE (1)	SE7806740L (da)
ZA (1)	ZA783327B (da)

1977
- 1977-06-13 FR FR7717990A patent/FR2394532A1/fr active Granted
1978
- 1978-05-23 GB GB21685/78A patent/GB1572689A/en not_active Expired
- 1978-06-09 AU AU36994/78A patent/AU515492B2/en not_active Expired
- 1978-06-09 BE BE188459A patent/BE867984A/xx unknown
- 1978-06-09 DE DE19782825388 patent/DE2825388A1/de not_active Withdrawn
- 1978-06-09 CA CA305,122A patent/CA1094566A/en not_active Expired
- 1978-06-09 LU LU79794A patent/LU79794A1/xx unknown
- 1978-06-09 DK DK258778A patent/DK258778A/da unknown
- 1978-06-09 NL NL7806269A patent/NL7806269A/xx not_active Application Discontinuation
- 1978-06-09 ZA ZA00783327A patent/ZA783327B/xx unknown
- 1978-06-09 NZ NZ187507A patent/NZ187507A/xx unknown
- 1978-06-09 JP JP7028878A patent/JPS545975A/ja active Pending
- 1978-06-09 IT IT24416/78A patent/IT1095286B/it active
- 1978-06-09 NO NO782027A patent/NO782027L/no unknown
- 1978-06-09 CH CH632778A patent/CH635081A5/fr not_active IP Right Cessation
- 1978-06-09 IE IE1169/78A patent/IE46988B1/en unknown
- 1978-06-09 SE SE7806740A patent/SE7806740L/xx unknown

Also Published As

Publication number	Publication date
IT1095286B (it)	1985-08-10
NL7806269A (nl)	1978-12-15
DK258778A (da)	1978-12-14
NO782027L (no)	1978-12-14
GB1572689A (en)	1980-07-30
CH635081A5 (en)	1983-03-15
AU3699478A (en)	1979-12-13
IT7824416A0 (it)	1978-06-09
DE2825388A1 (de)	1979-01-04
NZ187507A (en)	1979-10-25
LU79794A1 (fr)	1978-11-28
IE781169L (en)	1978-12-13
AU515492B2 (en)	1981-04-09
CA1094566A (en)	1981-01-27
FR2394532A1 (fr)	1979-01-12
BE867984A (fr)	1978-12-11
ZA783327B (en)	1979-06-27
JPS545975A (en)	1979-01-17
FR2394532B1 (da)	1980-01-18
SE7806740L (sv)	1978-12-14

Publication	Publication Date	Title
EP0193415B1 (en)	1991-06-26	Spiro-3-heteroazolidine compounds and salts thereof, their preparation and pharmaceutical agents thereof
SU1597096A3 (ru)	1990-09-30	Способ получени производных дифенилпропиламина или их фармакологически приемлемых солей
CY1444A (en)	1989-03-10	Salts of 2-(2,6-dichloroanilino)phenylacetic acit and their production
DE2027645A1 (de)	1971-12-09	Piperazinylalkyl chinazolon (4) den vate, Verfahren zu deren Herstellung und sie enthaltende Arzneimittel
IE56836B1 (en)	1992-01-01	Novel pharmaceutically active 1,2,3,4,4a,5,10,10a-octahydrobenzo(g)quinoline derivatives
DE2933649A1 (de)	1980-03-13	Imidazolderivate, sie enthaltende pharmazeutische zusammensetzungen
EP1382333B1 (en)	2009-02-25	Use of beta 3 adrenergic receptor agonists in the treatment of dysuria
EP0030861A2 (en)	1981-06-24	Isoquinoline acetic acids and pharmaceutical compositions thereof
WO1986005488A1 (fr)	1986-09-25	9-halogenprostaglandine et procede de production
FI61883B (fi)	1982-06-30	Foerfarande foer framstaellning av fysiologiskt aktiv 2-(2-fluor-6-trifluormetyl-fenylimino)-imidazolidin
DD233847A5 (de)	1986-03-12	Verfahren zur herstellung von methylendiphosphon-derivaten mit antireuhmatischen eigenschaften
NO834884L (no)	1984-07-02	Fremgangsmaate for fremstilling av farmakologisk aktive nitroalifatiske forbindelser
PT89120B (pt)	1993-04-30	Processo para a preparacao de novos derivados flavonoides 2-piperazinil-2-oxo-etileno substituidos
DD142048A5 (de)	1980-06-04	Verfahren zur herstellung von substituierten 2-phenylimino-imidazolidinen
KR860001578B1 (ko)	1986-10-10	3-티오메틸 파리딘 유도체의 제조방법
GB1565647A (en)	1980-04-23	Pharmacologically active compounds 4-substituted-imidazole-5-methanols
JPS6140268A (ja)	1986-02-26	イミダゾリン、その付加塩及びその製造方法並びにイミダゾリン又はその付加塩を有効成分とする医薬
US4775673A (en)	1988-10-04	Substituted acylpiperazinoquinazolines and pharmaceutical compositions containing same
CA1094566A (en)	1981-01-27	Imidazoline derivatives
US4157340A (en)	1979-06-05	N,N'-[Bis(N-cyanoguanyl)]cystamine derivatives
US3957785A (en)	1976-05-18	Bβ-Pyrimidino-aminomethyl-10α-ergoline and 10α-methoxyergoline derivatives
FI57589B (fi)	1980-05-30	Foerfarande foer framstaellning av blodtrycket saenkande 6-substituerade 3-karbetoksihydrazinopyridaziner
IE50570B1 (en)	1986-05-14	2-phenylamino-imidazolines-(2),compositions and processes for the preparation thereof
US3464990A (en)	1969-09-02	Barbituric acid derivatives substituted in the five position
DD201675A5 (de)	1983-08-03	Verfahren fuer die herstellung von cimetidin